South Chicago Vacations from ￥410,268

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The Latest South Chicago Vacation Packages

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jun 21 - Jun 27
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Every single person working at this facility was extremely polite and welcoming. I’ve stayed in so many hotels across the world and I have to say this was the best experience I’ve ever had staying at a hotel. Ordered food at 3am and it was fantastic. My cloths got folded in the short period of time my wife and I left the room and came back to a spotless room. Overall amazing experience. Will be staying here every time I come to Chicago.

Reviewed on Apr 16, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Jun 21 - Jun 27
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (3,485 reviews)
Very nice staff and great customer service! Would highly recommend the hotel bar, as the drinks and food were delicious! Only issue is that the deposit fee was not returned.

Reviewed on Apr 18, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Jun 21 - Jun 27
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (206 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar 16, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Jun 21 - Jun 27
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
YOGA AND POOL AND ELEGANT LUNCH AREA PLUS LOVE MY SUITE !!!!

Reviewed on Apr 17, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Jun 21 - Jun 27
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (965 reviews)
Friendly and helpful staff, super comfy rooms and bed! Walked everywhere- easy walk to museum/aquarium, shopping, dining etc. will definitely be back!

Reviewed on Apr 15, 2024

Prices and availability subject to change. Additional terms may apply.

Where to stay in South Chicago

Find the best South Chicago areas and neighborhoods for the activities you enjoy most. Learn more about South Chicago
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

South Chicago Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥17,444 per night from Apr 28 to Apr 29
￥17,444
per night
Apr 28 - Apr 29
7.6/10 Good! (6,547 reviews)
"I like it"

Reviewed on Apr 16, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥18,907 per night from Apr 22 to Apr 23
￥18,907
per night
Apr 22 - Apr 23
8.6/10 Excellent! (2,775 reviews)
Great hotel
"Hotel is in the best location. Right beside Michigan ave and the river walk is across the street. Excellent location. Short walk from most of the L trains and only a few extra blocks gets you to the Ohare blue line. Were given an early check in room which was nice and not expected. Staff were friendly. ..."

Reviewed on Apr 16, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥23,142 per night from Apr 30 to May 1
￥23,142
per night
Apr 30 - May 1
8.2/10 Very Good! (1,848 reviews)
"Property was very nice"

Reviewed on Apr 18, 2024

Eurostars Magnificent Mile
See all 3,936 properties in South Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a South Chicago vacation package cost?
Live it up in South Chicago from just ￥410,268. Choose from a wonderful selection of hotels, flights and rental cars to suit your travel style. You can score even more discounts when you add a few sightseeing activities to your vacation package.
How do I get a cheap travel package to South Chicago?
Combine your flights and hotels, toss in extras such as activities or a rental car, and save with a South Chicago vacation package. You won’t just pick up impressive discounts on your escape — you’ll have lots of choice within your reach too. When you book through Expedia, you can select from more than 550 partner airlines and 1,000,000 hotels around the globe. Your dream vacation starts right here, right now!
Where should I stay in South Chicago?
With so much to do in South Chicago, it’s a good idea to secure a room in a hotel close to its attractions. Calumet Beach, Calumet Park and Bronzeville Childrens Museum are some interesting ones to put on your must-see list.
How far in advance should I book my South Chicago vacation?
While not all airlines release ticket prices early, it’s usually possible to compare international fares on Expedia up to 12 months in advance. This is the time you can bag some fantastic bargains. If you’re purchasing tickets last minute, you might get lucky. Sometimes the cheapest prices emerge just weeks before departure.
What does an Expedia South Chicago travel package include?
From hotels and flights to car rentals, Expedia can help you craft a South Chicago package that fits you. Heading away for a week or longer? Consider a flight, rental car and hotel bundle. If you’re taking a quick break, a hotel and flight deal could suit you better. Tours and activities can be added after you’ve booked. Our packages make it a cinch to plan and save.
What should I know before booking a South Chicago travel package?
You’ll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and pick up fantastic discounts. You’re not restricted to hotels, though. We’ve got island resorts, cozy city apartments and everything in between!
Can I choose my airline with a South Chicago Expedia vacation package?
Yes, of course. Expedia has access to more than 550 airline partners around the world, so fly with the carrier that best fits your budget and traveling style.
If I'm not able to travel, can I cancel my South Chicago vacation package?
If your vacation plans in South Chicago have changed, it’s good to know that it’s possible to cancel your booking. If you made your booking less than 24 hours ago, you may be eligible for a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a cancellation fee. To find out more, check our Customer Service Portal.

Discover the most popular places to visit in South Chicago

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Navy Pier

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

￥23,662
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Pizza Tour

Chicago Pizza Tour

￥11,048
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.